“One may ride upon a tiger’s back but it is fatal to dismount.”—Ernest Bramah
Ride the tiger. That’s what we used to call working for a technology startup. It was a little like a gambling addiction. Objectively we knew the odds were against us. But we weren’t objective. We gave up sleep and personal lives (and occasionally basic hygiene) to stay on that tiger’s back. Our employee number—who was hired first, who had the best stock options, the most first-name access to the c’founders—was mentally tattooed across our brain, and haunted our dreams of the holy grail, the IPO.
I know, I know… and I have the (worthless) stock options to prove it. I know other serial-startup veterans who have papered their bathrooms with their old options. But like any gambler, we also knew the next Next Thing could be the one. And now and then, it even worked. Sort of. I never became a software millionaire, not even close. But I did get the occasional nice payout that bought a car or kitchen remodel.
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